


Pinnacle of Passion

by DRHPaints



Category: Bill Hader - Fandom, Doc Now - Fandom, Documentary Now - Fandom, Documentary Now! (TV 2015), Mr. Runner Up: My Life as an Oscar Bridesmaid
Genre: Blow Jobs, Boss/Employee Relationship, Cunnilingus, Explicit Language, Explicit Sexual Content, F/M, Office Blow Jobs, Office Sex, One Shot, Pining, Power Play, Smut, Under-Desk Blow Jobs, Use of the word Slut, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2020-12-10
Updated: 2020-12-10
Packaged: 2021-03-10 02:01:27
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,961
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27986610
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Wrapped up in an ongoing affair with studio head Jerry Wallach, secretary Betty McHenry enjoys their casual trysts in his office, but she wants something more.
Relationships: Jerry Wallach/Original Female Character(s)
Kudos: 9





	Pinnacle of Passion

**Author's Note:**

> Requested anonymously

“Miss McHenry?” Commanding voice radiating over the page, Betty perked her head up from the typewriter. “Could you come into my office, please?”

Pressing the button, Betty leaned down to the receiver. “Yes, Mr. Wallach. Right away.” Smoothing over her cherry-print dress, Betty’s heels clicked their way around the desk toward the door of Jerry’s office, legal pad and pen in hand for appearance’s sake as she swayed inside, giving the hallway a cursory glance before she locked the door.

“Why hello there, Miss McHenry.” Jerry lounged on the edge of his desk, hands in the pockets of his trim cut navy suit. Sharp jaw rolling through a smirk, Jerry’s cobalt eyes crawled over Betty’s curvaceous body, expression a hair short of lechery. “What do you have for me today?”

“Oh, well…” Betty took leisurely, almost dragging strides, well aware of how Jerry idolized her legs. Particularly in the skyscraper heels that brought Betty to his eye level as she grinned mischievously. “It seems you have a rather full itinerary today, Mr. Wallach.”

Nose flaring, Jerry’s weight rocked forward and he crossed his arms to resist the urge to go to her first as Betty continued her measured approach. “Is that so, Miss McHenry? Well...sounds stressful.”

“Yes sir.” Arriving at Jerry’s side, not with a crash but rather a delicate nudging of their desires, like two unmoored boats floating over a serene sea, Betty lifted her hand, threading Jerry’s tie seductively through her fingers, nails painted a blood red. “Maybe you need to...relax?”

“Mmm…” Not quite ready to relinquish control by touching her yet, Jerry’s prominent eyebrows popped and he shifted, unraveling his long legs, never parting from Betty’s lust-laden gaze. “I like the sound of that, Miss McHenry. What did you have in mind?”

Betty swiveled in, tucking her face into the crook of Jerry’s neck. Inhaling, she caught the crystalline, sharp notes of his aftershave, the sweet tang of the pomade used on his hairpiece, a not-so-well-kept secret around the Pinnacle Pictures lot. 

“Well…” Hand flowing down the wool of his suit, Betty pressed into Jerry until her breasts smushed against him, exhaling on his skin with alluring intent. “Perhaps you would like it if I…” Voice a sultry whisper, her fingers trickled over the bundle of Jerry’s crotch and she smiled victoriously when she felt his solid chest hitch beneath her taunt. “Suck this big cock of yours, Mr. Wallach?”

Jerry broke, big hands flying from his pockets to snatch at Betty’s waist, her perfectly coiffed crimson waves, relishing the idea that he might leave her a little disheveled for the rest of the workday as he latched onto her painted lips with a growl. 

At this point Betty knew well enough not to bury her hands in Jerry’s freakishly perfect chestnut hair, but the temptation was strong nonetheless as she draped her arms over his broad shoulders and Jerry left the desk, walking backwards to his leather chair.

Tongues weaving as he pawed hungrily over her dress, Jerry dipped beneath the cup of Betty’s bra to unearth an ample breast. Tweaking a nipple between his lengthy fingers, Betty knew she fit the stereotype as Jerry sat back and hastily unzipped his slacks. 

Betty knew as she sank to her knees that she was another slutty secretary, knew everyone would think she was trying to sleep her way to the top if they found out. Hell, Betty even knew that the reason Jerry hired her had nothing to do with her resume or her interview, but how her plump ass filled out her skirt as she left the room that day.

But as Betty shuffled down Jerry’s boxers enough to unearth his raging erection, she also noticed other things. Curious things. Sure, Jerry summoned her to his office at least once a day for some kind of erotic tryst or another. But he also paused every morning to ask Betty how she was doing. Head tilted and hands folded, Jerry actually seemed to care about the answer whenever she responded. Betty studied Jerry, watched as he questioned others, and the inquiries were polite at best, Jerry quickly proceeding to business and glossing over their words with a stellar smile and a hearty handshake. 

There were also instances in which the page didn’t indicate the siren’s song of Jerry’s libido (or, for once, a real secretarial task) but rather Jerry ordered lunch from his favorite deli in town and didn’t wish to eat alone. Though their shared meals consisted largely of Jerry talking about himself, the next picture he planned, an unfinished deal; he always bought a lemon bar specifically for Betty, knowing they were her favorite, and she munched in bemusement as he waxed on.

And so as the carpet chafed Betty’s kneecaps once again (how no one ever noticed the constant rug burn was beyond her) she wondered, fingers wrapping around Jerry’s burgeoning erection with a coy smile. 

“Mmm…” Jerry combed back her scarlet hair with one hand, relaxing back into the chair. “I love watching you work, Miss McHenry.”

Raising a teasing eyebrow, Betty’s tongue flashed out, hint of salt gracing her palette as she flicked over Jerry’s dewy slit. Warm mouth enveloping the wide head of his cock, her green eyes fluttered closed with a contented hum and she sucked luxuriously, stroking the girth of his shaft toward her lips.

“Mmm...fuck.” Head lolling back, Jerry’s hips surged forward, seeking the tight heat of Betty’s throat. “Yeah...suck me.” Betty worked her way down Jerry’s substantial length, breathing consciously through her nose, tongue pressed firmly to the underside of his straining cock before she began to bob.

Jerry’s huge hands started by massaging their way over her scalp, pelvis a steady row that squeaked the base of his elegant chair in sync with his audible breaths. But soon, as Betty’s cheeks hollowed and her saliva doused his paper-thin skin, Jerry twisted fists in her crimson tresses, thrusting with urgency.

“ _Oh fuck! Betty, yes! Your mouth! Fuck! Yes!”_ If Betty were forced to choose a favorite sound in the world it might be the tiny noise Jerry uttered between these words. Like a whimper falling down a flight of stairs, his solid chest would stutter, tone high and unusual as he drove his massive cock into Betty’s eager face.

“ _Fuck, Betty! Don’t stop! Yes! Fuck! Yes! Fu--”_

Knock sounding at the door, they both froze, Jerry continuing to hold Betty’s head in his lap. “Shit!” Blinking, Jerry looked down at her and swallowed before hurriedly motioning to the right. “Get under the desk!”

Betty dropped Jerry from her mouth, scooting beneath the mahogany canopy and making herself as small as possible before Jerry’s falsely cheery, authoritative voice called out. “Come in!”

“Jerry! Hey there!” Hearing Vice President Alan Triskell followed by the stout man’s lumbering footsteps, Jerry’s open legs, cock proudly perched between them, obscured the entirety of Betty’s vision in the dimness beneath the desk. “How are you today, you son of a bitch?”

“Oh, can’t complain…” Huge hand beckoning, Betty paused. “Well, I could, but who’s going to listen?” Jerry’s disarming chuckle boomed out and Betty shuffled forward, apprehensively angling Jerry’s cock toward her lips.

Alan laughed politely and Betty enveloped Jerry in the slippery solace of her mouth once more. “Too true. Well, anyway, I just wanted to pop by to see if you got those contracts for _Blondes, Blondes, Blondes, and a Millionaire?_ ”

“Ah, right…” One hand looping encouragingly around the back of Betty’s neck, the other rummaged through papers atop his desk and Jerry suppressed a moan. “Here you are. Pretty sure I signed them all.” 

With the flipping of pages as the only noise in the room, Betty was certain Alan would hear her slurping and stilled. But Jerry impatiently tapped her shoulder before his wide palm pushed down on the top of her head. Smiling around him, Betty wiggled into place, drawing up her arms. With one hand fondling his balls, the other poised securely around his shaft, Betty started to gobble Jerry’s huge cock as though she needed to convince him to award her a starring role in his next production.

Passing a wavering groan off as a clearing of his throat, Jerry’s voice eked out strangely. “So, um...those...those seem to be in order then?” Jerry puffed out his cheeks, releasing a huffing exhale as he ground his heels in the carpet.

“Hmm…” Alan scratched under his nose, Jerry’s left eye undergoing an incessant twitching as Betty sheathed his substantial length completely, undulating the practiced muscles of her throat with incredible velocity. “Yes, I think so. Good...thank you.”

“No problem…” Hands splayed over the desk, Jerry held his breath, invoking every ounce of self control not to shove his hips forward. “Just let me know if you need anything else.”

“Will do.” Alan smiled as Betty kept him ensconced, rapidly retracting only an inch or two as she tugged on Jerry’s balls and massaged her fingers into his perineum with the dexterity she knew drove him mad. “Well, see you later, Jer. Have a good one.”

“You too.” Jerry peeped, pinpricks of sweat breaking out on his forehead as he anxiously watched Alan’s loafers proceed toward the door.

As his back turned, Jerry offered the first relieving rock of his hips before Alan stopped. “Oh wait…” Arriving at the last page, Alan frowned. “You missed one. Just here.”

Almost crying out in dismay, Jerry hitched something resembling a smile on his pained face instead. “Oh did I? Well...here.” Snapping up a pen, Alan returned and Jerry dashed off his signature, barely legible with his shaking hands as his balls tightened and his cock throbbed over Betty’s sliding tongue. “There you go.”

“Thanks, Jer.” Alan started back but glanced at him, eyebrow raised. “You alright? You seem a little flushed.”

Face indeed a ridiculous shade of pink, Jerry nodded insistently. “Yes, I’m fine. Maybe a little warm. Nothing to worry about. Thank you, Alan.” Speaking far too quickly, Jerry inhaled, trapping the breath in his built chest and hoping to contain everything else.

“Alright, well...if you say so.” Giving a half smile, Alan waved and Jerry returned it, only to clap his fingers over his pink lips in what he hoped looked to be a half natural gesture. “Have a good day, Jer.”

“You too.” Cobalt eyes slamming closed and mouth dropping open, Jerry whiteknuckled the edge of the desk, first spurt of hot, salty cum shooting over Betty’s tongue as Alan swung the door open. Smothering his face until it latched, Jerry’s body jerked forward erratically, grunts wheezing from his broad frame as she greedily swallowed each drop until he melted back into the chair, spent and panting.

“Oh fuck…” Too weary to do up his slacks, Jerry slumped over the arms of his chair, gulping for breath. “That…” Meeting Betty’s emerald eyes, Jerry chuckled weakly. “That was cruel, Bette.”

“Excuse me?” Smirking, Betty hopped up on Jerry’s desk, one shapely leg folding over the other. “And whose idea was it for me to keep going under there? Hmm?”

Jerry’s contagious giggle, which surfaced only in his authentic moments of mirth, echoed through the room as he zipped up. “Fair enough.”

***

Bringing a fresh pitcher of water to Jerry’s desk, Betty couldn’t help but straighten the askew beer stein filled with pencils. Betty didn’t notice him entering the office until a strong pair of arms encircled her waist, Jerry’s supple pink lips brushing over the back of her neck.

“Mmm…” Jerry rubbed himself over the curve of Betty’s round ass with a delighted sigh, squeezing her tight. “I missed you today. Couldn’t stop thinking about you in my meeting…” Inching down her sleeve, Jerry’s mouth moved over Betty’s shoulder, unaware her face tensed as a sizable hand snuck up to her breast.

“Jerry, I…” Stilling his wrist, Betty sighed. “I wish you wouldn’t say things like that…”

Jerry paused, straightening up. “Why?” Betty turned and he tucked an errant scarlet strand behind her ear. “What’s wrong with that?”

“You don’t mean it.” Shaking her head, Betty leaned back against the desk for wont of a place to escape. “Just...don’t pretend that this...I know you don’t want more.” Green eyes locking into him, Betty swallowed. “And it’s...it’s cruel to make me think you could, Jerry.”

Arms falling, Jerry blinked. “I...don’t know what to say.”

Crossing her arms, Betty’s voice shrank to the ghost of a whisper and she studied the carpet. “You don’t have to say anything. It’s not like I don’t know.”

“I thought…” Jerry unraveled one of her hands, large thumb playing over Betty’s dainty fingers. “I thought you liked what we have.”

“I didn’t say I don’t.” Betty bit the inside of her cheek, “Just...I need the lines to be clear. Otherwise I’m...it gets too hard.”

Dropping his hold, Jerry fisted his hands in his pockets, chiseled features hardening. “So what? I can’t say that I think about you when I’m gone? That I miss you? What’s the big deal, Betty?”

Stung, Betty’s mouth opened. “Jerry, I...if you don’t understand why that’s unfair…”

Jerry narrowed his dark blue eyes, firm arms folding in an expression beyond infuriating. “Why don’t you explain it to me, Betty? Because I would think there would be dozens, maybe hundreds of women who would be glad to hear such a thing.”

“Oh, so what?” Standing, Betty’s hands fisted at her side, viridescent gaze flashing. “I’m supposed to be grateful? Because the great and powerful Jerry Wallach deigns to pay attention to me? Because you fuck me in your office whenever you want and treat me like some beckon call sex pot, is that it?”

Silent, Jerry looked her up and down, running his tongue over his teeth within his mouth before ticking his head to the side, prominent eyebrow arched. “Yes.”

Scoffing, Betty tossed up aggravated fingers, taking two stamping steps before Jerry’s strong arm caught her about the waist. “Hey…” Voice somehow unyielding iron and lushest cashmere, Jerry corralled Betty to himself, large frame molding around her reluctant anger. “I know you don’t want to walk away from this…” Tracing her lower lip, Jerry swept into Betty’s neck, kissing an intoxicating trail down to her collarbone as she stood stiffly. “Hmm? What’re you gonna do, Bette? Sit out there?” Fingers tickling down her spine, Betty shivered before Jerry’s large palm cupped her ass. “Watch me walk by everyday? Hmm?” Jerry drew the tip of his nose over her cheek, rotating his hips until his half hard cock bumped her hip. “Pretend you don’t want this?” 

Betty’s heel seemed to take a step toward Jerry of its own volition, her head leaning into his touch. “That you don’t want to come in here…” Aligning himself, Jerry backed Betty against the desk, capturing her lips, fingers playing with the red tendrils at the base of her neck until she relaxed beneath him and her mouth opened. Betty scooted back and Jerry carefully bunched her skirt up her creamy thighs, opening Betty’s legs with a knee. Resting their foreheads together, Jerry spoke in a tender, hopeful whisper. “Are you really going to pretend you don’t want me to fuck you, Betty?”

Nodding, Betty kissed along Jerry’s sculpted jaw, her ankles looping around the back of his legs. “Jerry…” Betty unbuttoned his jacket, hands sneaking around to caress his plush middle. “Fuck me.”

Clamping over her hips, Jerry dragged Betty to the utmost edge of the desk before yanking her panties to the side. Fingers petting over the lips of her pussy as he licked into her mouth, Jerry edged down the collar of Betty’s dress, pulling her breasts loose. Nipples hardening beneath his touch, Jerry coaxed into Betty’s pussy with aching precision, teasing her clit until she was wet and anxious, palming the outline of his cock roughly over his slacks and moaning into his mouth.

Slinking to the floor, Jerry’s pink lips dotted their way up Betty’s thighs, eyes an ocean of passionate purpose as he loosened his tie, unbuttoning the top of his shirt before surging forward with his crisp jaw. As Jerry’s long tongue spun, Betty clung to the edge of the desk to avoid taking hold of his faux locks whilst he hoisted her legs over the shelf of his shoulders. 

“ _Oh fuck! Jerry, yes!”_ Swirling her hips, Betty threw her head back as Jerry lapped at her swollen clit, two lengthy fingers sneaking inside to plunge against her g-spot until she dripped a stain onto the varnish. Flailing in her ecstasy, a shrapnel of pens clattered to the floor, nearly followed by the bulb lamp before a panting Betty caught the stem seconds before it crashed. 

“ _Jerry! Fuck! Yes! Don’t stop!”_ Writhing atop the desk, Betty’s body convulsed as though she were being electrocuted when Jerry’s pink lips surrounded her clit, sucking with abandon, her limbs juddering awkwardly with every flick of his tongue over the hypersensitive surface. “ _Jerry! I..! Fuck! Yes! Fuck!_ ” Every syllable accompanied by a darting hand and a fluttering eye, Betty cinched around his fingers and Jerry hummed into her sensitive flesh, emerging with a satisfied smile. 

Jerry stood, snapping up a couple of tissues to blot his shining face before unzipping his slacks to remove his thick cock. Swiping over Betty’s sopping folds, Jerry bent over, licking at a nipple before he brought his lips to her ear. “You want me to fuck you now? Huh, Bette?”

“Yeah…” Betty gasped, holding onto his love handles to guide Jerry inside. “Fuck me.”

If anything made it difficult not to fall in love with Jerry Wallach, it was the transformation he underwent as he entered Betty. His face, usually lacquered in plastic professionalism, would soften for a second, only for his expressive eyebrows to knit as the shutters of his lids closed and Jerry’s nose flared. Teeth clenching as he acclimated to the intense pressure, the muscle in his sharp jawline waved welcomingly as Jerry tilted forth.

But by far the part Betty adored the most was his sound. That low, long groan. Like someone prying open an ancient door, wood yearning to hold the seal, revealing a bevy of euphoric secrets the mind couldn’t begin to comprehend.

Swerving his hips to sense every inner surface, a rumbling chuckle burbled up from Jerry’s built chest as he wiggled a hand between them to thumb Betty’s clit. “See?” Smug voice paired with sparkling blue eyes, Jerry pecked Betty’s lips and came away smirking. “You can’t resist, Betty.” Massive cock driving forward, Jerry gyrated until he tamped against the spot that made her eyes go white and her heels shake. “You know you love it.”

“ _Yes!”_ Betty reached behind herself, using the opposite side of the desk to bear down onto Jerry’s barreling cock with wanton fury. “ _Yes, I love it! Fuck me, Jerry! Fuck me!”_

Pounding with a ruthless ferocity, Jerry fisted a hand in her crimson tresses, fusing their mouths together as he lost himself in the flickering heat of Betty’s drenched pussy. “ _Fuck, Betty! Yes!”_ Sheaf of papers slithering to the floor, Jerry hoisted one of her legs over his mountainous shoulders, knee climbing onto the desk for traction as he barreled inside. “ _Fuck! You feel so good, honey! Yes! Fuck!”_

Brain swatting away the term of endearment for the sake of their entwined ardor, Betty locked her ankles behind his back, arms encasing Jerry as she rapidly humped. “ _Fuck! Jerry! Yes! Keep going! Fuck! Fuck!”_

_“Oh Betty! Yes! Fuck! I--”_

The phone rang. Hips stuttering to a stop, Jerry stared. Ringing again, he glanced at Betty, her green eyes narrowing and lips pursing in a dare. Third jingle piercing the air, Jerry scoffed, shaking his head. Wide palm clapping over her mouth, Betty squealed indignantly as Jerry lifted the receiver. “Jerry Wallach, Pinnacle Pictures.”

Boiling, Betty glowered up at him, Jerry smiling at the voice speaking into his joined ear. Violently clenching the walls of her vagina in retribution, Betty chuckled under Jerry’s grip when she turned his, “Oh that sounds good,” into a question by shoving a high note into the last word. Deep blue eyes glittering, Jerry’s lip curled as Betty began milking his pleading cock from within. Cradling the phone against his broad shoulder, Jerry rammed his hips forward with a careless vehemenance, chuckling over the line. “Yes, that’s right. We expect to receive those contracts any day now…”

Redoubling his efforts over Betty’s clit, Jerry mastered his breathing to the best of his abilities as he nailed her to the desk with feverish mischief. Concentration fading as the tremors overtook her, Jerry’s sizable hand barely suppressed her shrieks. In a distant corner of her mind Betty supposed the caller would probably think they were filming a horror on the lot as she constricted around Jerry’s hammering cock, fingers clawing over his suit jacket.

“Alright, yes, great.” Jerry muffled the phone into his shoulder for a moment when an irrepressible groan burst from him at Betty’s squeeze. “ _Fuck…_ ” Whispering, Jerry blinked himself back to composure and sharply inhaled before returning to the call. “I’m sorry, what was that?” Hips continuing their frantic pace, Jerry nodded at the information received, lips a concentrated pout. “Right, well...just keep me posted, alright Madison? Thank you. Yes. Goodbye.” Slamming the receiver down with a relieved sigh, Jerry uncovered Betty’s mouth with a laugh. “Mmm…” Caressing her cheek, Jerry met Betty for a kiss, sharing breath for a moment as he rocketed inside. “Good job, Miss McHenry.”

Feet leaving the floor, Jerry joined Betty atop the desk, breathing shallow and thrusting frenetic as his handsome face began to contort above her. “ _Oh Betty! Yes! Fuck! I’m gonna cum! Fuck! Fuck!_ ” Tucking his square chin down, Jerry’s cobalt eyes shut and high, stammered grunts left his thrashing body as his motions became elliptical and uncoordinated. “ _Fuck! Betty! Betty!_ ” Scrambling to lasso her into his powerful arms, Jerry seized in silence, breath hot against Betty’s ear before he pumped a deluge of warm cum into her pulsing pussy, shuddering until they remained a useless compilation of entrenched limbs.

Lungs thirsty for oxygen, Betty turned her face away from the sweaty press of Jerry’s tall frame, hands rubbing over his wide back as he gathered himself. Tilting her chin, Jerry laced their mouths together with a prolonged sigh that jammed a merciless fist into Betty’s guts, tearing at her innards and reminding Betty of her foolishness.

Jerry rose, the two of them leaning against the desk as they did what they could to make themselves presentable. “So, Miss McHenry,” Jerry polished a hand over his synthetic hair with a grin. “Did you send the completed documents to Paramount like I asked?”

“Yes…” Avoiding Jerry’s eye, Betty jiggled herself back into her bra.

Clearing his throat, Jerry nodded. “And the contracts for the new starlet? What’s her name from out of Idaho? Did you finish those?”

Betty fluffed out her auburn locks, shoulders curled inward and barely bobbing her head. “Yes, sir…”

“Very good.” Jerry stood, walking around behind his desk to retrieve the fallen papers. Eyes on the floor as she shuffled away, Betty rubbed her elbow with the opposite hand. “In that case, Miss McHenry…” Popping up, Jerry’s businesslike manner faded, replaced by a disarmingly thoughtful expression as his sapphire eyes landed on Betty. “Perhaps...you’ll be free for dinner?”

Attempting, and failing, to ground her boundless smile, Betty nodded. “Yes, sir...Jerry. I’d like that.”

“Good.” Jerry came to his feet, tossing Betty a wink and a smirk. “About time I take you out to see more than the office ceiling.”

**Author's Note:**

> Thank you for taking the time to read! If you enjoyed this story, please leave a comment or come say hi on tumblr at fandomtransmandom. I also accept requests!


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